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Anion binding of short, flexible aryl triazole oligomers.

Publication ,  Journal Article
Juwarker, H; Lenhardt, JM; Castillo, JC; Zhao, E; Krishnamurthy, S; Jamiolkowski, RM; Kim, K-H; Craig, SL
Published in: The Journal of organic chemistry
December 2009

The flexible, electropositive cavity of linear 1,4-diaryl-1,2,3-triazole oligomers provides a suitable host for complexation of various anions. The binding affinities for various combinations of oligomer and anion were determined by (1)H NMR titrations. Effective ionic radius is found to be a primary determinant of the relative binding interactions of various guests, with small but measurable deviations in the case of nonspherical anions. Solvent effects are significant, and the strength of the binding interaction is found to depend directly on the donor ability of the solvent. A picture emerges in which anion binding can be effectively interpreted in terms of a competition between two solvation spheres: one provided by the solvent and a second dominated by a folded cavity lined with electropositive 1,2,3-triazole CH protons. Implications for rigid macrocycles and other multivalent hosts are discussed.

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Published In

The Journal of organic chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

December 2009

Volume

74

Issue

23

Start / End Page

8924 / 8934

Related Subject Headings

  • Triazoles
  • Solvents
  • Polymers
  • Organic Chemistry
  • Molecular Conformation
  • Magnetic Resonance Spectroscopy
  • Macrocyclic Compounds
  • Binding Sites
  • Anions
  • 3405 Organic chemistry
 

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Juwarker, H., Lenhardt, J. M., Castillo, J. C., Zhao, E., Krishnamurthy, S., Jamiolkowski, R. M., … Craig, S. L. (2009). Anion binding of short, flexible aryl triazole oligomers. The Journal of Organic Chemistry, 74(23), 8924–8934. https://doi.org/10.1021/jo901966f
Juwarker, Hemraj, Jeremy M. Lenhardt, José C. Castillo, Emily Zhao, Sibi Krishnamurthy, Ryan M. Jamiolkowski, Ki-Hyon Kim, and Stephen L. Craig. “Anion binding of short, flexible aryl triazole oligomers.The Journal of Organic Chemistry 74, no. 23 (December 2009): 8924–34. https://doi.org/10.1021/jo901966f.
Juwarker H, Lenhardt JM, Castillo JC, Zhao E, Krishnamurthy S, Jamiolkowski RM, et al. Anion binding of short, flexible aryl triazole oligomers. The Journal of organic chemistry. 2009 Dec;74(23):8924–34.
Juwarker, Hemraj, et al. “Anion binding of short, flexible aryl triazole oligomers.The Journal of Organic Chemistry, vol. 74, no. 23, Dec. 2009, pp. 8924–34. Epmc, doi:10.1021/jo901966f.
Juwarker H, Lenhardt JM, Castillo JC, Zhao E, Krishnamurthy S, Jamiolkowski RM, Kim K-H, Craig SL. Anion binding of short, flexible aryl triazole oligomers. The Journal of organic chemistry. 2009 Dec;74(23):8924–8934.
Journal cover image

Published In

The Journal of organic chemistry

DOI

EISSN

1520-6904

ISSN

0022-3263

Publication Date

December 2009

Volume

74

Issue

23

Start / End Page

8924 / 8934

Related Subject Headings

  • Triazoles
  • Solvents
  • Polymers
  • Organic Chemistry
  • Molecular Conformation
  • Magnetic Resonance Spectroscopy
  • Macrocyclic Compounds
  • Binding Sites
  • Anions
  • 3405 Organic chemistry